Whispering sweet lullabies into the ears of the viewers, Makura no Danshi presents the watcher with an experience of comfort. Each short episode features a different boy who will listen to the audience and hold them when they need it. There are boys to suit all tastes: Merry is a gentle brown-haired boy; Sousuke Tanaka is a mature working man; Kanade Hanamine is a high school student who acts tough, but is frightened by mere spiders; Eiji Kijinami is a sore loser who looks like a punk, but has a tender heart; the shy Ryuushi Theodore Emori loves stargazing; Yuu Maiki is a freshman with delusions of grandeur; Haruto Enokawa is an energetic 5-year-old who refuses to sleep without a bedtime story; Nao Sasayama is a hip college student that is addicted to his smartphone; Shirusu Mochizuki is a librarian that treasures both books and book lovers; Yonaga and Yayoi Chigiri are siblings who are learning flower arrangement; and Yuuichirou Iida is a humorous old man who runs an oden stall. Though the watchers may be troubled with various issues in life, these boys will softly talk about themselves and coax the audience members into revealing their problems. All the boys have kind hearts and will make the viewers feel special and loved.

Yabuki Joe is left downhearted and hopeless after a certain tragic event. In attempt to put the past behind him, Joe leaves the gym behind and begins wandering. On his travels he comes across the likes of Wolf Kanagushi and Goromaki Gondo, men who unintentionally fan the dying embers inside him, leading him to putting his wanderings to an end. His return home puts Joe back on the path to boxing, but unknown to himself and his trainer, he now suffers deep-set issues holding him back from fighting. In attempt to quell those issues, Carlos Rivera, a world renowned boxer is invited from Venezuela to help Joe recover.

Tousuke Rokudou is a first-year attending Aomori High, a school full of delinquents. He is often bullied by his classmates due to his incompatibility with their behavior, the only exceptions being his two good friends who are also social outcasts. Frustrated at the way they are treated, the three wish they could stand up and claim the fun, peaceful school life of their dreams. However, Tousuke's life takes a drastic turn when he receives a package from his late grandfather containing their family heirloom, a scroll said to possess the power to save him from impending danger. Upon holding the scroll, a sudden glow emanates, leaving a strange mark on Tousuke's forehead. Thinking that he's received the means to free himself and his friends from their daily treatment, Tousuke is shocked to find out that its effects are far different than what he had imagined. Although his bullying continues, he realizes that the mark from the scroll acts as a charm, capturing the hearts of delinquent girls—in particular, Ranna Himawari, the strongest of them all.

Miki Takekasa is an introverted high schooler who does not socialize with her classmates. However, she wants to know what fun really is, waiting for someone who could help her understand its true meaning. One day after school, she crosses paths with her classmate Aya Takayashiki, who takes her on a little adventure. Miki discovers wonders she had never seen before, opening a way to change her withdrawn life. On their way home, Miki and Aya see their class representative Midori Oono entering Saikoro Club, a store specializing in board games. After trying out a German board game, Miki soon understands the kind of fun she had been looking for: playing various games after school along with the friends and acquaintances she makes from her newfound pleasure.